BODIPY-Based Molecules, a Platform for Photonic and Solar Cells

Abstract

The 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based molecules have emerged as interesting material for optoelectronic applications. The facile structural modification of BODIPY core provides an opportunity to fine-tune its photophysical and optoelectronic properties thanks to the presence of eight reactive sites which allows for the developing of a large number of functionalized derivatives for various applications. This review will focus on BODIPY application as solid-state active material in solar cells and in photonic devices. It has been divided into two sections dedicated to the two different applications. This review provides a concise and precise description of the experimental results, their interpretation as well as the conclusions that can be drawn. The main current research outcomes are summarized to guide the readers towards the full exploitation of the use of this material in optoelectronic applications.

Mild Open-Shell Character of BODIPY and Its Impact on Singlet and Triplet Excitation Energies

“…For its part, the D configuration in BODIPY has a sensibly larger amplitude (2.53%) than that in the three linear acenes (Figure 4a). It is also worth noticing that the weight of the D configuration obtained with CASCI(2,2)/6-31G(d) is very close to the results obtained with highly correlated methods (Table 1), in particular to CASSCF (12,11)/cc-pVTZ. Moreover, while E D − E CS in BODIPY is computed as intermediate between Anth and Tet values, the CS/D coupling is much larger as the one dictated by the trend in the acene family (Figure 4b).…”

“…10 Overall, since the turn of the century, research interest in BODIPY has been in full upswing and new derivatives and applications are reported every year. 11,12 Moreover, during the last decade, BODIPY-based compounds have also shown to be able to efficiently generate triplet excitons if proper modifications are applied, for example, halogenation in the pyrrole rings. 13 Then, despite that in 2008 the observation of triplet excited states in BODIPY could be regarded as a novelty, 14,15 nowadays, BODIPY emerges as an excellent photosensitizer for photodynamic therapy.…”

“…BODIPY is the abbreviated name commonly employed for the widely used 4,4-difluoro-4-bora-3a,4a-diaza- s -indacene dye. − BODIPY and its derivatives present unique photophysical properties: large molar extinction coefficients at the ultraviolet–visible region, high fluorescence quantum yields, , tunable absorption and emission processes (with wavelengths ranging from visible to near-infrared) through chemical modifications, and high photostability and chemical stability. , These photophysical properties make BODIPY and their derivatives excellent luminophores for the application in bioimaging, data encryption/decryption, organic light-emitting diodes, and stimuli-responsive materials . Overall, since the turn of the century, research interest in BODIPY has been in full upswing and new derivatives and applications are reported every year. , Moreover, during the last decade, BODIPY-based compounds have also shown to be able to efficiently generate triplet excitons if proper modifications are applied, for example, halogenation in the pyrrole rings . Then, despite that in 2008 the observation of triplet excited states in BODIPY could be regarded as a novelty, , nowadays, BODIPY emerges as an excellent photosensitizer for photodynamic therapy. − …”

Asymmetric AZA-BODIPY with Optical Gain in the Near-Infrared Region

“…Therefore, the development of materials as well as device architectures with these particular properties has remained a challenge. One of the most promising molecules able to absorb and emit in the 700–900 nm region is 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) [ 16 , 17 , 18 ]. BODIPY can be described as a boradiazaindacene on account of the similarity with the all-carbon tricyclic ring having three p-delocalized rings (pyrrole, azafulvene and diazaborinin-type ring) and the numbering of substituents follows rule setup for the carbon polycycles (see Figure 1 a).…”

2-(4-(Dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro-1,2,4,5,3-tetrazaborinin-2-ium-3-ide

“…Various boron chelates are some of the most common fluorophores, finding widespread practical application in bioimaging [1], as molecular reporters and chemodosimeters [2,3], in sensors [4][5][6], in optoelectronic applications [7][8][9] and others. The most studied are BODIPY 1 [10][11][12] and their structural analogs 2 [13], BOPHY 3 [14], boron difluoride 1,3-diketonates 4 [15] and 1,3-ketoiminates 5 [16].…”